40 days in Hawaii Itinerary

40 days in Hawaii Itinerary

Created using Inspirock Hawaii trip itinerary builder

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Fly
1
Kailua-Kona, Island of Hawaii
— 6 nights
Drive
2
Volcano, Island of Hawaii
— 4 nights
Fly
3
Kihei, Maui
— 8 nights
Fly
4
Hanalei, Kauai
— 5 nights
Drive
5
Koloa, Kauai
— 4 nights
Fly
6
Honolulu, Oahu
— 12 nights
Fly

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Kailua-Kona, Island of Hawaii

— 6 nights

Heart of the Kona Coast

Thanks to its favorable location near a mountain range blocking the northeasterly trade winds, Kailua-Kona gets little rainfall, allowing adventure seekers and nature lovers a chance to enjoy over 300 days of sunshine each year.
Step off the beaten path and head to Mauna Kea and Pu'uhonua O Honaunau National Historical Park. Take a break from the city and head to Saddle Road and Honaunau Bay. You'll find plenty of places to visit near Kailua-Kona: Puukohola National Historic Park (in Kawaihae), Hapuna Beach State Recreation Area (in Puako) and Captain Cook (The Painted Church & Kealakekua Bay). And it doesn't end there: kick back and relax at Manini'owali Beach (Kua Bay), appreciate the views at Pololu Valley Lookout, experience rural life at Kona Joe Coffee, and tour the pleasant surroundings at Kahaluu Beach.

For maps, more things to do, reviews, and tourist information, go to the Kailua-Kona trip itinerary builder tool.

Durham to Kailua-Kona is an approximately 12.5-hour flight. Due to the time zone difference, you'll gain 5 hours traveling from Durham to Kailua-Kona. Traveling from Durham in November, expect Kailua-Kona to be much hotter, temps between 84°F and 73°F. Wrap up your sightseeing on the 30th (Tue) to allow time to drive to Volcano.

Things to do in Kailua-Kona

Parks · Outdoors · Nature · Historic Sites

Side Trips

Find places to stay Nov 24 — 30:

Volcano, Island of Hawaii

— 4 nights
Those who named Volcano opted for simplicity in choosing a title, taking the nearby fire-spewing Kilauea as a source of inspiration.
Eschew the tourist crowds and head to Hawaii Tropical Bioreserve and Garden and Punalu‘U Beach. Museum-lovers will get to explore Volcano Garden Arts and Pacific Tsunami Museum. Venture out of the city with trips to Hilo (Hilo Farmers Market, Rainbow Falls, &more) and Papakōlea Green Sand Beach (in Naalehu). There's lots more to do: hike along Kilauea Iki Trailhead, tour the pleasant surroundings at Kipuka Puaulu (Bird Park) Trail, take in the dramatic natural features at Thurston Lava Tube (Nahuku), and view the masterpieces at Volcano Art Center Gallery.

To find traveler tips, more things to do, photos, and other tourist information, refer to the Volcano visit website.

Traveling by car from Kailua-Kona to Volcano takes 2.5 hours. Alternatively, you can take a bus. Traveling from Kailua-Kona in November, plan for slightly colder nights in Volcano, with lows around 68°F. Finish up your sightseeing early on the 4th (Sat) so you can catch the flight to Kihei.

Things to do in Volcano

Parks · Outdoors · Museums · Shopping

Side Trips

Find places to stay Nov 30 — Dec 4:

Kihei, Maui

— 8 nights
Stretching over 9.7 km (6 mi) of pristine south Maui coastline, Kihei is the island's driest and sunniest region, making it a perfect location for water activities and beach leisure.
Get in touch with nature at Zipline and Napili Beach. Let the collections at Karen Lei's Gallery and Whalers Village Museum capture your imagination. Get out of town with these interesting Kihei side-trips: Haleakala National Park (Haleakala Crater, Pools at Ohe'o, &more), Kapalua (Kapalua Beach & D.T. Fleming Park) and Lahaina Banyan Court (in Lahaina). Next up on the itinerary: kick back and relax at Wailea Beach, head outdoors with Outdoor Activities, and stroll through Wailea Beach Path.

For reviews, more things to do, photos, and other tourist information, you can read our Kihei trip planner.

Getting from Volcano to Kihei by flight takes about 2.5 hours. In December, daily temperatures in Kihei can reach 82°F, while at night they dip to 66°F. Cap off your sightseeing on the 12th (Sun) early enough to catch the flight to Hanalei.

Things to do in Kihei

Parks · Outdoors · Beaches · Nature

Side Trips

Find places to stay Dec 4 — 12:

Hanalei, Kauai

— 5 nights
Hanalei is a census-designated place (CDP) in Kauai County, Hawaii, United States. Get outdoors at Na Pali Coast State Park and Ke'e Beach. Relax by the water at Hanalei Beach and Polihale State Park. Take a break from Hanalei with a short trip to Waimea Canyon State Park in Waimea, about 42 minutes away. There's much more to do: kick back and relax at Pali Ke Kua Beach (Hideaway s Beach), hike along Kalalau Trail, tour the pleasant surroundings at Anini Beach, and relax in the rural setting at Sugarloaf Pineapple Farm.

For more things to do, where to stay, traveler tips, and tourist information, go to the Hanalei holiday planning app.

You can fly from Kihei to Hanalei in 2.5 hours. In December in Hanalei, expect temperatures between 79°F during the day and 67°F at night. Wrap up your sightseeing on the 17th (Fri) to allow time to drive to Koloa.

Things to do in Hanalei

Parks · Outdoors · Beaches · Nature

Side Trips

Find places to stay Dec 12 — 17:

Koloa, Kauai

— 4 nights
Kōloa is an unincorporated census-designated place (CDP) in Kauai County, Hawaii, United States. Eschew the tourist crowds and head to Poipu Beach Park and Maha'ulepu Heritage Trail. Visit Shipwreck Beach and Kalapaki Beach for some beach relaxation. Go for a jaunt from Koloa to Kapaa to see Lydgate Farms Kauai Chocolate about 40 minutes away. There's lots more to do: take a tour by water with Boat Tours & Water Sports, take in the dramatic scenery at Wailua Falls, take in the dramatic natural features at Spouting Horn, and steep yourself in history at Menehune Fishpond.

To find photos, ratings, and other tourist information, use the Koloa trip maker.

You can drive from Hanalei to Koloa in 1.5 hours. In December, daily temperatures in Koloa can reach 79°F, while at night they dip to 67°F. Wrap up your sightseeing on the 21st (Tue) to allow time to fly to Honolulu.

Things to do in Koloa

Parks · Outdoors · Beaches · Nature

Side Trips

Find places to stay Dec 17 — 21:

Honolulu, Oahu

— 12 nights

Big Pineapple

In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Your inner history buff will appreciate USS Arizona Memorial and Makapuu Lighthouse Trail. Your cultural itinerary includes sights like National Memorial Cemetery of the Pacific and Waimea Valley. Venture out of the city with trips to Sharks Cove (in Pupukea), Kailua (Kailua Beach Park, Lanikai Beach, &more) and Swim with Dolphins (in Waianae). The adventure continues: enjoy the sand and surf at Waikiki Beach, buy something for everyone on your list at Ala Moana Center, see the interesting displays at USS Bowfin Submarine Museum & Park, and walk around Kapiolani Regional Park.

To see traveler tips, photos, ratings, and more tourist information, read our Honolulu trip website.

Traveling by flight from Koloa to Honolulu takes 2.5 hours. December in Honolulu sees daily highs of 82°F and lows of 69°F at night. Finish up your sightseeing early on the 2nd (Sun) so you can catch the flight back home.

Things to do in Honolulu

Parks · Outdoors · Beaches · Museums

Side Trips

Find places to stay Dec 21 — Jan 2:

Hawaii travel guide

4.4
The Aloha State
An archipelago of hundreds of volcanic islands located in a geological hot spot in the middle of Pacific, Hawaii offers diverse natural scenery and a warm tropical climate. The six major islands open to tourism draw visitors with their sun-drenched public beaches and craggy natural trails. Thanks to their mid-Pacific location, the islands boast a vibrant native culture influenced by both North America and Asia. You can spend your vacation basking in the modern comforts of the big hotels, but to experience the true spirit of these islands, remember that real Hawaiians live outdoors. Encounter nature by surfing, swimming, fishing, and picnicking, or join a guided tour across the ancient lava flows to the top of Hawaii's rugged volcanic peaks.